2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester

Base Information

Chemical Name:2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester
CAS No.:205693-54-5
Molecular Formula:C₇₃H₉₆O₁₁Si
Molecular Weight:1177.64
Hs Code.:

Synonyms:2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester

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Chemical Property of 2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester

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Technology Process of 2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester

There total 22 articles about 2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

: 127-08-2
potassium acetate

: 205693-53-4
2-Benzyloxy-6-{(R)-16-[(2R,3S,4S,5R)-3,4,6-tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-trifluoromethanesulfonyloxy-hexanoyloxy]-heptadecyl}-benzoic acid benzyl ester

: (2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid (R)-16-(3-benzyloxy-2-benzyloxycarbonyl-phenyl)-1-methyl-hexadecyl ester

: 205693-54-5
2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester

Guidance literature:: In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;
DOI:10.1021/jo9800098

Reference yield: 74.0%

: 127-08-2
potassium acetate

: 205693-53-4
2-Benzyloxy-6-{(R)-16-[(2R,3S,4S,5R)-3,4,6-tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-trifluoromethanesulfonyloxy-hexanoyloxy]-heptadecyl}-benzoic acid benzyl ester

: 205693-54-5
2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester

Guidance literature:: In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1021/jo9800098

Reference yield:

: 13-tetradecenyl magnesium bromide

: 205693-54-5
2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 86 percent / CuCl(COD) / tetrahydrofuran / -78 - 20 °C

2.1: 94 percent / imidazole / dimethylformamide / 20 °C

3.1: [9-H-9-BBN]2 / tetrahydrofuran

3.2: 86 percent / NaOMe; KBr / PdCl₂(dppf) / tetrahydrofuran / Heating

4.1: NaH / dimethylformamide / 0.5 h / 0 - 20 °C

4.2: 92 percent / dimethylformamide / 3 h / 20 °C

5.1: 93 percent / K₂CO₃ / dimethylformamide / 4 h / Heating

6.1: 89 percent / TBAF / tetrahydrofuran / 15 h / 20 °C

7.1: 1468 mg / DMAP / CH₂Cl₂ / 16 h / 0 - 20 °C

8.1: 1007 mg / DDQ / CH₂Cl₂; H₂O / 3.5 h / 0 - 20 °C

9.1: 90 percent / pyridine / CH₂Cl₂ / 0.25 h / 0 °C

10.1: 18 percent / dimethylformamide / 2 h / 0 - 20 °C

With pyridine; 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; CuCl(COD); In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Addition / 2.1: silylation / 3.1: Addition / 3.2: Suzuki reaction / 4.1: Metallation / 4.2: Ring cleavage / 5.1: Etherification / 6.1: desilylation / 7.1: Esterification / 8.1: Oxidation / 9.1: triflation / 10.1: Cyclization;
DOI:10.1021/jo9800098